Acetic Acid → HCID 10196601, compound

HRID 902618Notes

Reaction equation

[Cl:1][C:2]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]([CH2:20][CH:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1.[C:37](O)(=[O:39])[CH3:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:32]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]([CH2:20][CH:21]([O:28][C:37](=[O:39])[CH3:38])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2-hydroxy-2-phenyl-ethyl)amino]propoxy}-phenyl)acetic acid (Example 15 b) in anhydrous toluene (5 ml) was treated with acetic acid (3 mg). Polymer bound triphenylphosphine (30 mg, 3 mmol/g) was then added, and the mixture reacted for 15 min. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate(10 mg, 0.05 mmol) was added dropwise. After stirring at RT overnight the crude mixture was filtered and the solid washed with 10 ml toluene. After concentration of the filtrate in vacuo, the crude product was purified by HPLC to give the title compound as an oil (20 mg, 75%). MS (ESI) 563.8 (M+H)+.

Workup

additionwas then added
customthe mixture reacted for 15 min
filtrationwas filtered
washthe solid washed with 10 ml toluene
customAfter concentration of the filtrate in vacuo, the crude product was purified by HPLC

Sources & evidence

ORD record: ord-75100fd4370d47fbbe70f4e398b76d1f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365085B2

Reaction notes

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